Unfortunately the concern you voiced about DD when he was hired have been realized. I think he has spent too much on relievers ( I hate big$ contracts and particularly ones to relievers ) both in contracts and in prospect currency. Yeah, you can't keep them all and yes most of them never amount to much or flame out. Still, he has cast off most of this team's chips for a bunch or arms whose best days may be behind them or are just not worth it.
I'm not losing sleep about the 2021 cliff because I believe some useful talent currently in the system will manifest itself and there will be other draftees that bring some value.
But if the Sox do not win a WS in the next two or three years it will be seen as a failed effort chasing a tittle with a huge payroll and few native pieces to build further on.
Bailey, Hanrahan, Smith, Thornberg.....none of them has ever worked out to date. Spending big money on BP arms is mostly a waste of time and money when decent lower cost arms can be developed and sourced otherwise.